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As a young man, Prince Oswald was a prolific prankster and troublemaker, and was responsible for the deaths of both Serene and Samson through negligence, but as a second son he was not expected to ascend to the throne. Nevertheless he schemed his way to the throne, murdering his well-liked elder brother Prince Ewan and later, his father (but not before taking his brother's betrothed, Lady Lyrica, as his wife, and having her assassinated).

The reign of King Thorn was nasty, brutish, and short. His first act as king was to execute Lord Humphrey Faren for accusing him of murdering his father, declaring all traitors would be punished without delay. Early in his reign, Krytan King Thorn proposed a treaty to the centauran tribes, but the centaurs rejected its terms as unfavorable. Later, famine and drought struck Kryta, but the high taxes drove some peasants to theft and others to starvation. King Thorn rounded up all citizens who were even suspected of theft and cut off their hands. He kidnapped the father of the IstaniPrincess Zola and ransomed him for her hand in marriage, but had her executed when he grew tired of her, sparking a war with Istan (in which Kryta was ultimately victorious).

He had eight wives in total; the other known wives include Estrella, who was killed by Oswald when he put her in a coffin full of rats and dumped it into the sea, and Henrietta, who was killed by his heir, Prince Edrick. There was also Edrick's mother, whose name is still unknown, who was beheaded on his birthday. Oswald viewed his son to be a disappointment, and after a failed coup attempt on the final night of his rule, stuffed his son's mouth with candy corn and had him locked in the Shell of Insanity.

His tyranny came to an end in approximately 825 AE when an angry mob stormed Castle Thorn, ending his earthly rule. The rebels intended to kill his eighth wife and son as well during the assault, ending the Thorn dynasty, and beseech his cousin to take the throne and plead forgiveness. Worried that he would try to return using his magic, his killers hid his body parts in boxes and buried them in locations scattered across Tyria, obscuring their locations with magical seals.

Although unable to return to Tyria due to the seals (except at Halloween, at which he would make an annual appearance), Thorn rose to notoriety within the Underworld, coming to rule a sub-realm of his own. In 1079 AE, the ascension of Queen Salma to the throne of Kryta broke one of the seals, and his Lunatic Court set about attempting to break the rest of them, so that he may be as powerful in Tyria as he was in the Underworld. A selection of artifacts from his life was gathered, and a suitable vessel for his spirit was obtained from a mausoleum. The political climate was also prepared for his return, inciting his arch-rival Palawa Joko into swearing to "flood valleys and enslave nations" to get his vengeance on Tyria, and defeating the only being capable of telling as good a joke as the Mad King, Qwytzylkak. But the rituals had not freed King Thorn but his favored steed, Mister Gum Drops, and the Lunatic Court returned to the drawing board chastened.

After his court's failure, the Mad King's presence influence was not felt for a long time, and he became a folklore used to scare children. However, in 1325 AE, over two centuries after his court's failure, the Mad King made a dramatic return, shattering the Lion's Court in the Grand Piazza of Lion's Arch and assaulting the citizens with insidious pranks and terrible jokes, attempting to break free into Tyria. His return was opposed by Magister Tassi, and foiled by heroes who ventured straight into the Mad King's realm, defeating him in his own game as well as in battle.